Cesium carbonate → HCID 66698950, compound

HRID 1095966Notes

Reaction equation

HRID 1095966 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:26])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:25])[C:9]([OH:24])([C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][N:18]=[CH:19]2)[C:10]([F:13])([F:12])[F:11].[CH2:27]([O:29][C:30](=[O:39])[C:31]1[CH:36]=[CH:35][C:34]([CH2:37]Br)=[CH:33][CH:32]=1)[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C>[CH2:27]([O:29][C:30](=[O:39])[C:31]1[CH:36]=[CH:35][C:34]([CH2:37][O:26][C:4]2[CH:5]=[CH:6][C:7]([CH:8]([CH3:25])[C:9]([OH:24])([C:14]3[CH:23]=[CH:22][CH:21]=[C:20]4[C:15]=3[CH:16]=[CH:17][N:18]=[CH:19]4)[C:10]([F:11])([F:13])[F:12])=[C:2]([Cl:1])[CH:3]=2)=[CH:33][CH:32]=1)[CH3:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 954261Ethyl 4-(bromomethyl)benzoateHCID 574213013-Chloro-4-(3,3,3-trifluoro-2-hydroxy-2-isoquinolin-5-yl-1-methyl-propyl)-phenol

Product 1

HCID 66698950HCID 66698950, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 3-chloro-4-(3,3,3-trifluoro-2-hydroxy-2-isoquinolin-5-yl-1-methyl -propyl)-phenol (40 mg) in N,N-dimethylacetamide (1 ml) were added ethyl-4-(bromomethyl)benzoate (18 mg) and cesium carbonate (23 mg). The mixture was stirred for 1 h at room temperature. Ice water was added and the mixture was extracted with EtOAc. The organic phase was washed with water and dried (MgSO4). The product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>0:1) to give the title compound (28 mg) as an off-white solid. MS (m/e)=544.2 [M+H+].

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. customThe product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>0:1)

Sources & evidence

ORD record
ord-b39a8e4314e1474c85758a3b9be6ca9c
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

Loading…